Bravo this philosophy will serve you well in life ! I work in an industry with low renumeration. for many years I followed your perscribed path. I have used the Smith Maneuver as you have described ... and been building a portfolio for years. Fairfax has been a core holding for 20 years. like you, i perceive risk differently, risk only exists where you are not doing the math and worst case plan.(margin of safety) Today I. showed the wife the accounts, she said "that's too much, more than we need" not actually huge, but enough that retirement is covered for all possibilities with a wide margin of safety. What i am saying is have this frugal and analytical bent is more important than picking the right horse . The highest risk is not having a big picture plan.